https://hdporn.video/tags/ifuckedtheboss-com/ Sat, 18 Apr 2026 05:58:33 UTC https://hdporn.video/video/184472/the-ass-fucked-boss-is-rita-daniels/
Rita Daniels, one of our favorite GILFs ever, is the busty boss who catches her young employee, 24-year-old Rocky, talking about her on the phone. He thinks he can say whatever he wants because he's speaking Spanish and he doesn't think Rita understands. But she does, especially when he tells whoever he's talking to that his boss has big tits and he wants to fuck her. Put it this way: No matter what language you're speaking, if you say, ""My boss has big tits and I want to fuck her,"" and the boss you're referring to is Rita Daniels, she'll understand. Rita is fluent in multiple languages of fuck talk. Anyway, before long, lucky Rocky is playing with Rita's big tits and eating her hairy pussy (it's usually shaved; not this time). Then she's sucking his dick, one of the things she does best (the horny-as-hell look on her face when she's downing dick is one of the best things about Rita) and sitting on his cock and then taking his cock in her tight asshole. And then he's cumming on her face. Nobody-and we mean nobody-looks better than Rita with cum dripping down her face. Rita is a mother and a grandmother. If her kids only knew! Actually, they do. ]]> Mon, 15 Sep 2025 00:00:00 UTC https://hdporn.video/video/184472/the-ass-fucked-boss-is-rita-daniels/ https://hdporn.video/video/184457/he-s-late-but-he-s-on-time-for-the-boss-s-pussy/
When this video opens, you might say to yourself, ""What the fuck? What are those two chicks, who obviously aren't 40-something, doing in my video?"" But then 44-year-old Gina shows up, and everything starts to click. She's wearing a tight leopard-skin mini, a skin-hugging top and fuck-me pumps. Turns out she's the boss of this eating and drinking establishment, and she's pissed off. Levi, the hired help, is late for his shift again. ""You have to respect me and do whatever I tell you to do,"" Gina tells Levi. ""I think you look hot,"" he says. ""Is that respectful?"" ""Maybe,"" Gina says, and then she loosens up in a hurry. He fingers her hairy pussy and feeds his cock into her mouth. At the end, he shoots his load into her wide-open mouth. Gina is not the typical mature woman who suddenly discovers sex when she turns 40. A star of well over 200 fuck films since she was in her 20s, Gina says, ""I'm easy. I just want hot, steamy sex."" Gina isn't into any fetishes. She doesn't want you to tell her that she's a bad girl, and she has no desire to fuck you with a strap-on. ""I love to suck cock and I love getting fucked hard and long,"" she said. ""I've been horny for as long as I can remember, and I don't think that will ever change. It's just me."" ]]> Mon, 01 Sep 2025 00:00:00 UTC https://hdporn.video/video/184457/he-s-late-but-he-s-on-time-for-the-boss-s-pussy/ https://hdporn.video/video/184599/bethany-gets-a-creampie-from-her-boss/
Bethany James, a 64-year-old divorcee, plays out a favorite fantasy: boss fucks his sexy employee. The boss is Mr. DeSergio. The sexy employee is, of course, Bethany. In real life, Bethany is a retired executive who worked for the State of Ohio. She was more the boss, less the employee, and she enjoyed more than her share of business trips during which she picked up strange men, took them back to her hotel room and fucked them. ""I once picked up two fabulous men in a downtown hotel in Chicago and took them back to my room,"" she said. ""We fucked all night, then we never saw each other again."" Here, Bethany fucks her boss, filling her mouth with his cock then getting fucked in her pussy. She's wearing pantyhose, for those of you who are into that (we know a lot of you are), and at the end, Bethany gets a creampie in her pussy. ""Nice and messy,"" Bethany said afterwards. ""Just how I like it."" A creampied 60plus...just how we like 'em! ]]> Mon, 04 Aug 2025 00:00:00 UTC https://hdporn.video/video/184599/bethany-gets-a-creampie-from-her-boss/ https://hdporn.video/video/184492/luna-s-employee-bonus/
Luna Azul, 60, pulls the old, ""Lady boss catches the young employee at the copy machine and decides to fuck him because he's making copies of pictures of her pussy,"" trick. You never heard of that trick, did you? Well, you might have heard about a hot female boss, and you might have heard about male employees checking her out behind her back and talking about how much they'd like to fuck her. Well, that's what's been going on in Luna's office, but what the boys don't realize is that Luna wants to fuck them, too. Some of the best parts of this scene come early on, such as when Luna sits on the desk in the middle of the copy room and tells her employee to eat her pussy right then and there, and if they get caught, so what? She's the boss. Another good part is when the employee realizes Luna is wearing pantyhose and the only way to get to her pussy is to tear a hole in them. Which he does, and Luna doesn't mind that she's going to have a hole in her pantyhose for the rest of the day, and who knows? Maybe she'll fuck another employee. Of course, there's that messy cunt that Luna will have to deal with, too, because, yes, the boss takes a creampie in this one. That's what's called an employee bonus. ]]> Mon, 21 Jul 2025 00:00:00 UTC https://hdporn.video/video/184492/luna-s-employee-bonus/ https://hdporn.video/video/184468/jewel-s-internal-affairs/
There are good bosses and there are bad bosses. Jewel is one of the good ones. After saddling her new employee with a tough assignment that has him stressed out and working late, she has him back to her office for what she calls ""a little de-stressing session."" And what does that involve? Hey, it's Jewel! You know exactly what that involves. Tit-sucking. Cock-sucking. Deep fucking on Jewel's desk and office couch. But if a man really needs to de-stress-if he really needs to take a load off, so to speak-he needs to shoot his load deep in a GILF's pussy. And that pussy belongs to Jewel. Yep, it's an internal cum shot and creampie for Jewel, and by the time the dude pulls his cock out of her 60something pussy, her cunt lips are sticky and the cum is pouring down her ass cheeks. ""I love creampies,"" Jewel said. ""It's so natural. It's the way most people fuck, right?"" Most people, yes, but not most porn people, which is what makes this so special. Jewel, 61 and married, does something that even a lot of experienced porn sluts won't do. But don't call Jewel a slut. She's a lady. A lady who deserves your cum. ]]> Mon, 07 Jul 2025 00:00:00 UTC https://hdporn.video/video/184468/jewel-s-internal-affairs/ https://hdporn.video/video/184520/busty-bosses-with-pierced-pussies-love-hard-cocks/
Thanks for picking me up and bringing me home,"" 54-year-old Deb says to Tony at the start of this scene. ""Would you like to come in for a while?"" She pushes him down onto the bed. You see, he's already ""in."" ""Is this your bedroom?"" he asks stupidly. ""How do you like it?"" she asks. ""I love it,"" he says. ""You're gonna love what we're gonna do with it. Or in it,"" she says. ""I've had my eye on you for a long time,"" she says. He can't believe it, although what did he expect when this busty MILF accepted his offer of a ride? Did he think she thought he was being a Good Samaritan? Ah, we get it! She's his boss! And he's been flirting with the young girls in the office, perhaps not even thinking about fucking the boss, not knowing about her big, fake, DDD-cup tits and all those piercings on her pussy, not knowing she's horny for cock all the time. Miss Deb is a wife from Spokane, Washington. She's a MILF. A super-MILF, we say. ""I wear low-cut, tight tops to show off my tits and short skirts to show off my legs,"" Miss Deb said. ""When you have great legs, they should be shown off. I've noticed that men don't get that far, nor do they make eye contact."" Nope. They just fuck her. ]]> Mon, 23 Jun 2025 00:00:00 UTC https://hdporn.video/video/184520/busty-bosses-with-pierced-pussies-love-hard-cocks/ https://hdporn.video/video/184557/sindy-swank-means-business/
Now this is how you run a business meeting! You're the boss, but Sindy Swank thinks she knows what's best for your company, even though it's been in your family for 54 years. You tell her, ""We're going to do things the traditional way,"" but she counters with, ""These days, women have the power."" Now you've got her exactly where you want her because she's gonna prove it. And how is she gonna prove it? You know how! This 54-year-old divorcee from Virginia bends over and says, ""Pull my skirt off,"" then demands, ""Lick my ass, now!"" She thinks she's teaching you a lesson in business, but this is exactly what your cock wanted all the time. ""Put four fingers in there,"" she demands. ""Put four fingers in my pussy! Fuck me!"" So you slide four fingers into her pussy and when she says, ""Keep fucking me! Don't stop fucking me!"" the truth is you have no intention of stopping. Because soon, it's gonna be your turn. So she gets down on her knees and sucks your cock and balls. By now, she thinks you're coming around to her way of running a company, but in fact, this is what you had in mind all along. She really stuffs her face into your balls, and then you fuck her mouth, pumping, pumping. When she sucks your balls, your rod brushes against her cheek, and if you don't get into her pussy soon, your balls are going to explode. ""Best fucking meeting we've ever had in this company,"" you say as you fuck her on the table, and this time, you mean it. ""Oh, yes, you're the best boss I've ever had!"" Sindy says as your balls slap against her asshole. Don't you know it. ""I'm proud of my cock-sucking skills,"" Sindy said. ""I practice a lot."" She has sex four or five times a week and is very assertive. One time, she hosted a swingers party and only men showed up. ""It turned into my first gang bang,"" Sindy said. ""But not my last."" ]]> Mon, 09 Jun 2025 00:00:00 UTC https://hdporn.video/video/184557/sindy-swank-means-business/ https://hdporn.video/video/184435/chanel-makes-the-gardener-s-cock-grow/
I'm a lady in the boardroom, a slut in the bedroom,"" said 50-year-old Chanel Carrera. ""Isn't that what men want?"" Here, Chanel is a slut in her backyard garden and in the bedroom, which is definitely what we want. We don't know how Chanel makes things grow in the garden, but she definitely can make our cocks grow in the bedroom or anywhere else. Chanel was born in New York City, lives in Boston, Massachusetts and has our favorite marital status: divorced. That's code for horny as fucking hell. She lists one of her hobbies as ""going to swingers' parties in which I'm the centerpiece."" But she says this is the most exciting thing she's ever done. ""Being 50 and still being able to turn men on and have them want to look at my pictures is the most exciting thing I could have ever imagined,"" she said. ""Do you see how wet my pussy is? That's because the whole time, I couldn't stop thinking about all you horny guys at home looking at me while you have your cocks in your hands, stroking them and getting harder."" She must be clairvoyant. ]]> Mon, 26 May 2025 00:00:00 UTC https://hdporn.video/video/184435/chanel-makes-the-gardener-s-cock-grow/ https://hdporn.video/video/184533/work-that-boss-s-ass/
Jamie is a hard-driving, bitchy boss, and she's making a lot of demands. This poor guy has a lot of work to do and not much time to do it, but he's distracted by Jamie. You see, she's sitting in the office in a very unprofessional manner. Her legs are crossed, and this poor shlub can see the top of her stockings and her thighs, and Jamie's talking about work, and all he wants her to do is work his cock. ""Are you paying attention to me?"" Jamie asks. ""Have you written down anything that I said?"" She takes his notepad to see what he's been writing, and she's shocked. ""Wow, 'I wanna pound that ass?' That's what you wrote?"" Jamie says, aghast. ""'Do you deep throat? I want your ass?' That's what you've been taking notes about the whole time?"" Now emboldened, the guy says, ""I also wrote, 'I want you to suck my cock right now.'"" This kind of stuff can get a guy fired...if his boss is somebody other than Jamie. ""You know what I think?"" Jamie tells him. ""I think you're a very dirty boy. I like dirty boys."" Jamie found out about us from a friend she knows online. She has a long list of fetishes and is a very kinky woman. No one really knows how wild her private sex life is. ""I like sex multiple times a day,"" Jamie said. ""I can be submissive or bossy depending on my partner of the moment. I'm kind of an exhibitionist. I like men or women getting sexually aroused by watching me. In a video, I can get thousands of people hot."" She definitely does that. ]]> Mon, 12 May 2025 00:00:00 UTC https://hdporn.video/video/184533/work-that-boss-s-ass/ https://hdporn.video/video/184465/severance-pay-layla-s-pussy/
In real life, Layla Redd, a 41-year-old divorcee from Maryland, is an educator. An assistant principal in a high school. At least she used to be one. She lost her job. Here, she's a boss at a big company. Unfortunately, times are tough, and she has to fire some of her employees. Unfortunately for Juan, he's one of the ones to go. Fortunately for Juan, he's going to get a goodbye fuck before he leaves. No wonder the unemployment rate is so high! Men are getting fired on purpose so they can fuck their sexy female bosses on the way out! Okay, that's probably not the reason. But if Layla were your boss, it could be the reason. ""I'm a swinger,"" Layla said. ""I love having sex with other men and having my boyfriend watch. I dress conservatively because I had to at my old job, so a lot of people would never guess at the real me. They'd never think that I would pose nude and have sex on-camera."" Layla has perfect B-cup tits that she covers in those conservative clothes. Not surprisingly, she always wears a bra. That's what keeps her tits so beautiful. Her hobbies are traveling, reading and ""being lazy,"" but she says she likes men who aren't afraid to take chances. In this video, Juan isn't afraid to take a chance. Layla obviously likes that about him. That and his cock. And if you're asking us which came first, her attraction to his cock or her attraction to his risk-taking, well, we just haven't thought it through that deeply. And neither should you. ]]> Mon, 28 Apr 2025 00:00:00 UTC https://hdporn.video/video/184465/severance-pay-layla-s-pussy/ https://hdporn.video/video/184555/the-lawn-boys-dp-kelly-leigh/
Kelly Leigh is a no-nonsense woman, so when she drops the drinks she brought out for her lawn care boys, she makes up for it by dropping to her knees and sucking their cocks. Would most women do this? No. But most women are not Kelly Leigh, who sucks dick like she's making love to it, enjoys being called ""a fucking dirty whore"" and takes cocks in her ass as casually as most women take it in their pussies. ""I want your fucking cock in my ass!"" she screams. There's DP action here, too, because Kelly is that kind of woman. A porn star, of course, but one who doesn't do it for the money. She does it for the sex. And if you need proof of that, just watch this video. ""I love acting like a slut,"" Kelly said. ""I love getting DP'd and sucking balls and doing all the things that women my age aren't supposed to be doing. Sucking two cocks, getting fucked in my ass, cum facials. I love it all, and the sleazier the better. I feel proud when I hear people say that I'm the sluttiest porn star they've ever seen, but in my mind, I can be even sluttier!"" Kelly also said, ""I laugh when I see those porn prima donnas who are worried about their hair getting messed up during a scene. It's sex! Your hair's supposed to be flying everywhere. Besides, it's gonna be full of cum soon, anyway. That's the whole idea!"" ]]> Mon, 31 Mar 2025 00:00:00 UTC https://hdporn.video/video/184555/the-lawn-boys-dp-kelly-leigh/ https://hdporn.video/video/184311/the-deal-isn-t-sealed-but-rita-s-holes-are-stuffed/
Rita Daniels is the boss, and she calls her star salesmen into her office. She's wearing a short skirt, and her big tits are straining her blouse, which is distracting enough. The guys think they're in trouble. Sales are down. She tells them they're going to have to do a little tag-teaming. ""We're good at tag-teaming,"" they say. She asks them what she can do to boost their morale. Will it take a bonus? A free trip? Rita's tits, pussy and asshole, perhaps? Yeah, that'll do it. You see, the boys have been talking about fucking Rita's 62-year-old ass. And Rita has been thinking about getting her 62-year-old ass fucked by her star salesmen. She wants them to work as a team? They can do that. They can jam her mouth with their cocks. One can fuck her pussy while the other feeds her his cock. They can take turns fucking her asshole. Because teamwork is all about sharing. Motivated? Damn, right they're motivated. Motivated to tag-team Rita's ass. But sales? That's another story. ]]> Mon, 03 Mar 2025 00:00:00 UTC https://hdporn.video/video/184311/the-deal-isn-t-sealed-but-rita-s-holes-are-stuffed/